Artificial fragrance and flavoring ingredients have long been used to enhance, improve, or modify the aroma or flavor in perfume compositions, pharmaceutical and medicinal products, and a wide variety of foodstuffs and consumable materials. Artificial fragrance and flavoring ingredients have numerous and significant advantages over natural ingredients, such as uniformity of aroma and flavor and decreased tendency to spoil during storage. Accordingly, close reproduction of floral, fruit-like and vegetable aromas and flavors has been the subject of long and continuous searches and efforts.
Research in this area has lead to the development of a number of oxygen and sulfur containing compounds which have desirable aroma and flavor characteristics. For example, the use of 3,7-dimethyl-octa-2,6-dienyl mercaptan as an odorant and flavorant has been described in U.S. Pat. Nos. 3,896,175 and 3,996,387. This compound possesses an aroma which smells like berry and grapefruit.
British Patent No. 1,546,283 describes the cyclogeranyl mercaptan possessing a grapefruit-like odor.
U.S. Pat. No. 4,600,576 relates to dimethyl octadienyl mercapto esters as food flavorants which have grapefruit and citrus-like flavor characteristics.
European Patent 0054847 A2 describes certain cyclic terpenes which are thiol substituted and used to flavor certain foods.
Morrison, "Synthesis of 4-and 5-Benzothiazol-2-yldithio-2,6-dimethylocta-2,6-diene and Other Models for Pendent Groups in the Sulfur Vulcanization of Natural Rubber", J. Chem. Soc. Perkin Trans. I pp. 101 to 106 (1984) describes certain thioacetates, thiols and related compounds used for the sulfur vulcanization of natural rubber. No reference is made to usefulness in perfumes or flavors as organoleptic agents.
Gauthier et al., "A Mild and Efficient Synthesis of Thiolesters from Alcohols", Tet. Lett. Vol. 27, No. 1, pp. 15 to 18 (1986) relates to the synthesis of numerous thioesters without addressing an ultimate utility for the compounds.
Volante, "A New, Highly Efficient Method for the Conversion of Alcohols to Thiolesters and Thiols", Tett. Let. Vol. 22, No. 33, pp. 3119 to 3122 (1981) describes the conversion of alcohols to thiols and thioesters at the three position in 3B cholesteryl compounds.
U.S. Pat. No. 2,993,857 relates to certain cyclic thiol substituted terpenes having organoleptic properties.
U.S. Pat. No. 4,478,865 describes sulfur containing cycloterpenes which possess organoleptic properties of a fruity, especially grapefruit, character. Research pertaining to these compounds is also described in E. Demole et al., "176.1-p-Menthene-8-thiol: A Powerful Flavor Impact Constituent of Grapefruit Juice (Citrus paradisi MacFayden)", Helv. Chim. Acta, 65:1785-1794 (1982).
The use of 1,3-oxathiane and 1,3-oxathiolane derivatives as perfuming and flavoring agents has been described in U.S. Pat. Nos. 4,220,561 and 4,262,030.
The isolation and identification of several sulfur containing compounds which possess passionfruit-like and grapefruit-like organoleptic properties is described in W. Pickenhagen and E. Demole, Natural Trace Sulfur Compounds and their Contribution to Fruit Flavors, IXth International Congress of Essential Oils, Singapore (Book #3 p. 1-7) March, 1983.
In their pure state, many of the above compounds, especially the sulfur containing compounds, have very powerful and unpleasant odors. Examples of sulfur containing materials which are malodorants are t-butylthiol or mercaptoacetic acid. Accordingly, due to the fact that the chemical mechanisms of odor perception are currently not well understood, reproduction of certain fruit-like and floral odors is difficult and unpredictable. Thus, materials which will closely simulate such odors are highly desirable.
The availability of such artificial ingredients is expected to render alternative food sources, such as processed foods and non-meat sources of protein, more attractive and palatable, by improving the flavors and aromas. Thus, chemical compounds which closely imitate or reproduce the aromas and flavors of a variety of tropical and citrus fruits and floral odors are highly desirable.
One object of the present invention is to develop novel compounds possessing fruity or floral odors.
Another object of the present invention is to develop a process for synthesizing sulfur containing hydrocarbon compounds which possesses useful organoleptic properties.
Yet another object of the present invention is to provide oxygen and sulfur containing compounds for use as fragrance and flavoring ingredients. These compounds can enhance, improve, alter, or modify the fragrance properties of perfumes and perfumed articles, and the flavor properties of foodstuffs, beverages, gums, mouthwashes, toothpastes, pharmaceutical preparations, medicinal products, and tobacco or tobacco products by adding thereto an effective amount of the above formula.